When to book Hotels and Transportation

This will be my first trip to Thailand with my boyfriend and we’re looking to spend about two weeks there. We’re still in the early days of planning, but are ready to buy our flight tickets to Bangkok for beginning of November (we want to make it for Loi Krathong).

Because that’ll be the “busy season”, when should we start booking for hotels/hostels? Would we be okay waiting until we get there to find places on the fly? We want to keep our costs down but enjoy some luxuries outside of the hotel. Any suggestions?

We also wanted to travel between the northern part and the southern beaches. Would you recommend trains or flights? I know flying would be faster, but I think we’d enjoy the experience and scenery with trains (and possibly costs).

I recently traveled to Thailand last Oct-Dec with my boyfriend and we were in Chiang Mai for Loi Krathong. When we left in Oct, we didn’t have anything booked except our flight into Bangkok. It’s easy to book hotels on-the-fly. You’ll be totally fine to wait until you get there. You can often walk up to places and negotiate price with the front desk clerk and this way you get to check out the place before you book too. If we didn’t simply walk up to a place, we used TripAdvisor to find most of our hotel accommodations and also used other traveler’s recommendations. Be sure to book a few weeks to a month in advance during the days of Loi Krathong, as many accommodations are full during this time.

As for traveling from North to South, we flew from Chiang Mai to Phuket, but traveled by bus and boat the rest of the way around the Andaman and Gulf of Thailand coasts.

If you’re going up north I’d recommend Chiang Mai (go here for Loi Krathong…make sure to go to the university if you want to experience all of the YouTube videos and images you see online for the festival) and be sure to spend a couple nights in Pai (1-hour bus from Chiang Mai). Khao Sok National Park (right between the two coasts) is awesome if you guys are up for hiking through a rainforest. I liked the Gulf coast better than the Andaman coast. Koh Tao is a fabulous little island with some of the most stunning views in all of Thailand.